Three weeks ago I came up with this crazy idea with my boss to hustle my way to South by Southwest Interactive (SXSW) at no cost. Easy right? Sort of. Anyway, with our goal in mind, it was time to figure out how to get it done.

What follows is a personal story of how I ended up on a train to Portland this morning as the first leg of a mission to Texas. I’m confident that you can take some learnings from my experience for ways to pitch your big shiny ideas, get them noticed, and green-lit.

What’s this all about?

Today I start a 5 day journey from Vancouver to Austin, Texas. Sure my main goal was to find a way to get to SXSW, but as I look out the window, i’m realizing it’s about the journey, not the destination.

SXSW is the go-to event for nerds and tech geeks looking to make waves in the industry. Major media brands like Twitter owe their fame in part to launching at SXSW. Every year, it’s a ners’ arms race to figure out which hot new startup will take over.

My employer, HootSuite, sent a team of 10 down last-year. And I knew this year would be similar. The handful who do get to go are the envy of the rest of the company because SXSW is a geek’s paradise.

Being the realest I am, I figured my name would not be on the list for 2013. The lucky chosen few tend to be more higher up established peeps.

That is where this crazy idea started. Could I hack my way to SXSW?

Enter the train & a primer on sending the treacherous cold email

My boss, DaveO, is your modern day Jack Kerouac – the train idea was his. I remember him saying a month ago: “reach out to Amtrak and let’s see if we can train you down to sxsw.”

With that, I got my creep on and tried to find find someone at Amtrak who might be interested in hearing what I had to say.

The basic plan was this: if you provide travel arrangements, I will tell the story of my journey by blogging, producing videos, and just about every other form of media out there.

Once I found someone, it was time to extend the olive branch with the ultimate email.

When you’re in this situation, you need to take the perspective of the person you’re targeting with your pitch. What emotions are they going to feel getting a random email?

and how can you use this information to choose the right words in order to get a reaction?

Once you figure this out, you can start crafting the copy for your email.

Make it about them

The email you send isn’t about you. It is about accommodating the random person reading the email. Make it as short, concise, and as easy to read as possible. Bulleted lists, bold words, and short, well written sentences are your friend.

Note: I probably take this a bit too far, as i’ve been told my emails on occasion are… a bit too the point (true story).

But for the sake of pitching, you really need to cut through the crap and get to the point. Especially if you’re pitching to someone who gets hundreds of emails daily.

What do I have to offer to help them and why is this pitch worth reading?

I had two things going for me with which to start: a unique story and the offer of online exposure. My story is an uncharacteristic journey to SXSW by train. Because, who in their right mind would spend 70 odd hours on a train for what would be a 5 hour flight?

Not only that, there’s also a secondary story about showing the masses how awesome train travel can be.

In terms of online exposure, i’m lucky in that I have the HootSuite name and platform: including the blog and social media accounts. This went a long way into crafting my pitch.

I know decision makers usually want stats and numbers. So I played ‘ball’ and shared the type of buzz I’m confident I can get going around the campaign.

You never know, this thing could go viral. Eh?

Perceptions are important. Figure out what someone wants, that is your end-goal. Once you have this info, you can work to figure out how to craft your pitch and get what you want.

Opportunities are out there, make them your own

My little anecdote is nothing special, but I hope it shows you what you can pull off with an idea and a little elbow grease.

A month ago, I had no chance of going to SXSW. After a couple of emails, the next thing I know, i’m on conferences calls with people from Washington DC and New York pitching my vision for this thing.

I told them how I wanted to tell the story of the timelessness of train travel, how awesome and enjoyable the trip can be. Because after all, train travel definitely is not the sexy choice among younger North Americans.

I will say that i’m friggin stoked for this adventure. Sitting on a train now about to pass through the border into Washington State, I have to pinch myself because I can’t beleive this is actually happening.

#5Run in three states

You read correctly. The other cool thing I just realized is that i’ll be able to high five runners in three different states over the next 10 days!

Three out of 50 ain’t bad, but I definitely plan to knock off all 50 states in due time.

Nice, wish I knew who at Amtrak to talk to about HugTrainUSA, my hugging journey around the US every year during the holidays – I’ve been doing it for 4 years with zero support from them
Have a great time – happy to help if you need to know anything about train travel and the routes you,re taking!